Copending U.S. patent application Ser. No. 687,318, filed May 26, 1976 by Elena M. Bingham and William Joseph Middleton, which is a continuation-in-part of U.S. patent application Ser. No. 597,502, now abandoned, discloses certain novel 3-fluorobenzodiazepines of the formula: ##STR1## where X is Cl, Br, NO.sub.2, or CF.sub.3 ;
Y is H, Cl, Br or F; PA1 D is H, hydrocarbyl of 1-4 carbons, --CH.sub.2 CF.sub.3, --CONHR, --CH.sub.2 CH.sub.2 NR.sub.2, or --CH.sub.2 CH.sub.2 NR.sub.2 .multidot.A, where R is alkyl of 1-4 carbons and A is a pharmaceutically suitable acid; PA1 B is O; or PA1 B and D together is .dbd.N--N.dbd.C(R')-- where R' is H or C.sub.1 -C.sub.4 alkyl, PA1 Y is H, Br, Cl or F; PA1 R is hydrocarbyl or halohydrocarbyl of 1-8 carbons; PA1 R.sup.1 is H or CH.sub.3 ; PA1 R.sup.2 is alkyl of 1-6 carbons; PA1 Z is I, Cl, Br, CF.sub.3 SO.sub.2 O--, FSO.sub.2 O--, CCl.sub.3 SO.sub.2 O-- or CH.sub.3 OSO.sub.2 O--; and PA1 Z.sup.1 and Z.sup.2 are Cl or Br. PA1 Y is H, Cl, Br or F; and PA1 Z.sup.1 is Cl or Br; PA1 B = o; PA1 x = cl, PA1 D = h; PA1 d = c.sub.1 --c.sub.3 alkyl; PA1 X = cl and D = H; PA1 X = cl and D = C.sub.1 -C.sub.3 alkyl. PA1 X = cl or Br; PA1 Y = h, cl, or F; PA1 D = h, --ch.sub.3 or --C.sub.2 H.sub.5 ; and PA1 B = o. PA1 X = cl or Br; PA1 Y = h or F; PA1 D = ch.sub.3 ; and PA1 B = o.
And the use of such compounds as tranquilizers, muscle relaxants and sedatives in mammals. In addition, Bingham and Middleton disclose a process for making such compounds by reaction of the corresponding 3-hydroxybenzodiazepine with a dialkylaminosulfur trifluoride as follows: ##STR2## where R.sup.3 and R.sup.4 are a primary alkyl group of 1-4 carbons or taken together are --(CH.sub.2).sub.4 -- or --(CH.sub.2).sub.5.
In addition, copending U.S. patent applications Ser. Nos. 807,074; 807,075; and 807,076, filed simultaneously herewith together disclose an improved process for preparing such 3-fluorobenzodiazepines, which improved process can be summarized schematically as follows: ##STR3## where X is Br, Cl, NO.sub.2 or CF.sub.3 ;